A wooden gazebo by a pond with a large tree trunk nearby.

Shelter Island Hotel Guide - Hotels with Pool in Shelter Island, New York

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Check availability on Shelter Island Hotels with Pool

Tonight
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

Our top choices for Shelter Island hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and a view of boats.
A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

1. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
€189
includes taxes & fees
1 Nov - 2 Nov
The Harbor Front Inn
Property amenity
Property amenity
Bar (on property)
Terrace/patio

2. Shelter Island House

Shelter Island House
Shelter Island Heights
  • Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
€204
includes taxes & fees
5 Oct - 6 Oct
Shelter Island House
A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.
A spacious room with wicker furniture, large windows, and a view of the sea.
A beach bar with wooden chairs and a small table, overlooking the sea.
A coastal building with large windows, a deck, and a view of the sea at sunset.

3. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
€220
includes taxes & fees
2 Nov - 3 Nov
Sound View Greenport
Outdoor pool
Room
Terrace/patio
Beach

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
€270
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums
A poolside area with a hat and towel on a lounge chair.
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.
A modern house with a deck, outdoor seating, and a fire pit.
A modern bathroom with a black bathtub, white sink, and shower area. There are framed pictures on the wall and a potted plant on the counter.

5. North Fork Resort

North Fork Resort
Greenport
€270
includes taxes & fees
5 Oct - 6 Oct
North Fork Resort
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A waterfront property with a large house, multiple boats docked, and lush greenery.
A hotel lobby with a sofa, chairs, tables, and a large window.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

6. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
  • Swim into serenity at this charming Sag Harbour retreat with a seasonal outdoor pool and balcony views.
€222
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
A poolside area with lounge chairs and yellow umbrellas.
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.
A wooden shower enclosure with a tiled wall, a showerhead, and a toilet visible through the door.
A wooden desk with drawers, a chair, a lamp, and a framed picture on the wall.

7. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
€291
includes taxes & fees
1 Nov - 2 Nov
Oyster Estate
A large indoor swimming pool with multiple lanes, safety signs, and a tiled wall with hexagonal patterns.
A wooden deck with Adirondack chairs and tables, overlooking a scenic landscape.
A modern bathroom with a glass shower enclosure, a bathtub, and a wall-mounted faucet.
A coastal pathway with a wooden bridge leading to a green sports court.

8. Ocean Vista Resort

Ocean Vista Resort
Amagansett
  • Oceanside sanctuary provides splendid private beach access and indoor pool oasis.
€129
includes taxes & fees
5 Oct - 6 Oct
Ocean Vista Resort
Outdoor pool
Terrace/patio
Room
Living area

9. East Hampton House Resort

East Hampton House Resort
East Hampton North
  • Seasonal outdoor pool creates a refreshing escape at this hotel, with tennis courts and gardens adding to the resort atmosphere.
€161
includes taxes & fees
2 Nov - 3 Nov
East Hampton House Resort
A modern indoor swimming pool with marble walls and a tiled floor.
A spacious hallway with high ceilings, arched columns, and chandeliers.
A garden pathway with a fence, illuminated by string lights, leading to a building.
A wooden bench with a large planter in front.

10. Montauk Manor

Montauk Manor
Montauk
  • Refreshing hilltop retreat with year-round pool access and sweeping ocean vistas.
€145
includes taxes & fees
2 Nov - 3 Nov
Montauk Manor
View all properties

Choose what matters most at hotels with a pool in Shelter Island

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Shelter Island Hotel Reviews

Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Room was clean,staff was amazing food wasn't good for us."
Edrise 1-night trip
Posted 4 hours ago
Montauk Yacht Club
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"The property was definitely worth a five-star rating and the views of the Bay were tremendous! The rooms were very clean and the beds were super comfortable. I had a wonderful breakfast looking out over the water. It was magical"
Melanie 1-night trip
Posted 1 day ago
Water's Edge Resort & Spa
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Such a great spot! Clean, easy access, everything you need!!"
Christian 3-night trip
Posted 2 days ago
Ocean Resort Inn
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Beachcomber was wonderful loved it"
elizabeth 3-night trip
Posted 3 days ago
Beachcomber Resort at Montauk

Frequently asked questions

What are some accommodation options with pools in Shelter Island?
Pier Blue Inn Old Saybrook - Essex: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool and a private beach. Gurney's Montauk Resort & Seawater Spa: Hotel, 1-minute walk from The Hamptons Beaches. Provides a sauna, a seasonal outdoor pool and free self parking. Offshore Montauk: Features a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa: Offers a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Hotel, 1-minute walk from The Hamptons Beaches. Features sunloungers, an indoor pool and complimentary wireless Internet access.
What is there to see and do in Shelter Island?
Surround yourself with nature at Mashomack Preserve and Sunset Beach. Discover sights such as Shelter Island Historical Society, Wades Beach and Crescent Beach during your stay.
When is the best time to book a hotel with a pool in Shelter Island?
You may want to think about accommodation that has an outdoor pool if you'll be visiting Shelter Island in the hottest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be what you want if you come to town during the coldest months of January, February or March, when the average temperature is 3°C.